Fansided

30 highest career MLB salaries

By Nathaniel Reeves

Aug 12, 2016; Bronx, NY, USA; New York Yankees designated hitter Alex Rodriguez (13) waves to the fans after playing his final game as a Yankee against the Tampa Bay Rays at Yankee Stadium. The Yankees won 6-3. Mandatory Credit: Andy Marlin-USA TODAY Sports
Aug 12, 2016; Bronx, NY, USA; New York Yankees designated hitter Alex Rodriguez (13) waves to the fans after playing his final game as a Yankee against the Tampa Bay Rays at Yankee Stadium. The Yankees won 6-3. Mandatory Credit: Andy Marlin-USA TODAY Sports /
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MIAMI – APRIL 13: Gary Sheffield #11 of the Atlanta Braves stands at bat during the game against the Florida Marlins at Pro Player Stadium on April 13, 2003 in Miami Florida. The Braves defeated the Marlins 7-1. (Photo By Eliot J. Schechter/Getty Images)
MIAMI – APRIL 13: Gary Sheffield #11 of the Atlanta Braves stands at bat during the game against the Florida Marlins at Pro Player Stadium on April 13, 2003 in Miami Florida. The Braves defeated the Marlins 7-1. (Photo By Eliot J. Schechter/Getty Images) /

20. Gary Sheffield, $168,008,550

One of the most feared hitters of his era, Sheffield remains in the top 20 after signing the then-largest contract extension in MLB history in the late 1990s.

The nephew of Mets legend Dwight Gooden, Sheffield originally came up as a highly touted prospect in the Milwaukee Brewers organization. Sheffield didn’t do much in four seasons with the Brewers before being traded to the San Diego Padres in 1992, when he went off for 33 home runs and 6.2 WAR.

San Diego traded Sheffield to Miami the next season, and he was unable to replicate that level of overall production again until 1996.  The Marlins rewarded Sheffield with a six-year, $61 million extension the next spring, surpassing the MLB record for total money on a contract previously set by Albert Belle.

After helping Miami win the 1997 World Series, Sheffield would play for the Los Angeles Dodgers and Braves over the rest of the deal, which ran through 2003. Sheffield wasn’t done in free agency quite yet, as the Yankees, Detroit Tigers and Mets gave him a total of nearly $75 million from 2004-2009 up until his retirement at age 40.

While Sheffield might fall just short of Hall of Fame induction, he was well worth the $168 million with 509 career home runs and a lifetime OBP that falls just short of .400.

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